#------------------------------------------------------------------------------ #$Date: 2026-06-03 23:54:34 +0100 (Wed, 03 Jun 2026) $ #$Revision: 306181 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721073.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7721073 loop_ _publ_author_name 'Niessen, Nicolas' 'Adjieufack, Abel Idrice' 'Tumanov, Nikolay' 'Wouters, Johan' 'Champagne, Beno\^it' 'Berionni, Guillaume' 'Bijouard, Kajetan' _publ_section_title ; Accessing chiral NHC-boranes by abstraction of C6F5 from the B(C6F5)4− weakly coordinating anion ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D5DT02919H _journal_year 2026 _chemical_formula_moiety 'C17 H19 B N2' _chemical_formula_sum 'C17 H19 B N2' _chemical_formula_weight 262.15 _chemical_name_common 'N-benzhydryl-N?-methyl-imidazolylidene borane' _chemical_name_systematic (1-benzhydryl-3-methyl-1H-imidazol-3-ium-2-yl)trihydroborate _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _atom_sites_solution_secondary dual _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2025-10-16 deposited with the CCDC. 2026-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.4888(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.0181(2) _cell_length_b 8.9143(2) _cell_length_c 17.1117(3) _cell_measurement_reflns_used 9930 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 68.2586 _cell_measurement_theta_min 4.9872 _cell_volume 1525.32(5) _computing_cell_refinement 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_data_collection 'Bruker Instrument Service vV6.2.16' _computing_data_reduction 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_structure_refinement 'SHELXL-2019/4 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w-scans' _diffrn_radiation_monochromator 'multilayer mirror' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_unetI/netI 0.0472 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 20661 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.253 _diffrn_reflns_theta_min 5.179 _exptl_absorpt_coefficient_mu 0.506 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). "Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination" J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.142 _exptl_crystal_description block _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.230 _refine_diff_density_max 0.174 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.0237(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/4 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 2790 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0450 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.2908P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1240 _refine_ls_wR_factor_ref 0.1261 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2647 _reflns_number_total 2790 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5dt02919h2.cif _cod_data_source_block nt1362_KB249 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7721073 _shelx_shelxl_version_number 2019/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.793 _shelx_estimated_absorpt_t_max 0.893 _shelx_res_file ; TITL cu_nt1362_KB249 in P2(1)/n nt1362_KB249.res created by SHELXL-2019/3 at 17:06:14 on 01-Feb-2024 CELL 1.54178 10.01810 8.91430 17.11170 90.0000 93.4888 90.0000 ZERR 4.00 0.00020 0.00020 0.00030 0.0000 0.0006 0.0000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H B N UNIT 68 76 4 8 ACTA CONF LIST 4 TEMP 23 SIZE 0.48 0.32 0.23 L.S. 10 BOND $H REM LIST 6 FMAP 2 PLAN 20 WGHT 0.061300 0.290800 EXTI 0.023669 FVAR 0.34420 0.33923 N1 4 0.677621 0.255178 0.433162 11.00000 0.03944 0.05636 = 0.04241 -0.00706 0.00553 -0.00078 N2 4 0.591052 0.146855 0.330586 11.00000 0.04894 0.06060 = 0.04704 -0.00970 0.00275 -0.00451 C1 1 0.573292 0.074195 0.254089 11.00000 0.07064 0.08953 = 0.05861 -0.02644 -0.00082 -0.01049 AFIX 127 H1A 2 0.509925 0.130026 0.221331 21.00000 -1.50000 H1B 2 0.540828 -0.026095 0.260541 21.00000 -1.50000 H1C 2 0.657457 0.070932 0.230152 21.00000 -1.50000 H1D 2 0.628882 -0.013451 0.253352 -21.00000 -1.50000 H1E 2 0.597979 0.142670 0.214142 -21.00000 -1.50000 H1F 2 0.481350 0.045643 0.244530 -21.00000 -1.50000 AFIX 0 C4 1 0.708693 0.192909 0.364617 11.00000 0.04680 0.04279 = 0.03972 0.00094 0.00340 0.00208 C5 1 0.853655 0.163690 0.599868 11.00000 0.05255 0.05239 = 0.05782 0.00008 0.00347 0.00779 AFIX 43 H5 2 0.919948 0.128804 0.568722 11.00000 -1.20000 AFIX 0 C6 1 0.845283 0.106988 0.674445 11.00000 0.07395 0.06348 = 0.06703 0.01613 -0.00010 0.00954 AFIX 43 H6 2 0.906243 0.034995 0.693296 11.00000 -1.20000 AFIX 0 C7 1 0.747622 0.156272 0.720789 11.00000 0.07980 0.06681 = 0.04995 0.01152 0.00114 -0.01102 AFIX 43 H7 2 0.741690 0.117019 0.770813 11.00000 -1.20000 AFIX 0 C8 1 0.657951 0.264285 0.693209 11.00000 0.06574 0.06635 = 0.04881 -0.00882 0.01511 -0.00847 AFIX 43 H8 2 0.591401 0.297674 0.724585 11.00000 -1.20000 AFIX 0 C9 1 0.667170 0.322971 0.618688 11.00000 0.05155 0.05495 = 0.04866 -0.00390 0.00719 0.00559 AFIX 43 H9 2 0.607668 0.397091 0.600636 11.00000 -1.20000 AFIX 0 C10 1 0.764676 0.271846 0.570768 11.00000 0.04226 0.04446 = 0.04231 -0.00416 0.00150 -0.00055 C11 1 0.775502 0.329814 0.488075 11.00000 0.03638 0.05362 = 0.04157 -0.00514 0.00256 0.00238 AFIX 13 H11 2 0.864253 0.300582 0.472311 11.00000 -1.20000 AFIX 0 C12 1 0.767535 0.499783 0.480226 11.00000 0.03640 0.05371 = 0.04306 0.00119 0.00600 0.00032 C13 1 0.831396 0.589869 0.537541 11.00000 0.05027 0.05871 = 0.05640 0.00164 -0.00529 -0.00560 AFIX 43 H13 2 0.875129 0.545505 0.581129 11.00000 -1.20000 AFIX 0 C14 1 0.830637 0.744454 0.530494 11.00000 0.05776 0.05766 = 0.07808 -0.00375 -0.00017 -0.01301 AFIX 43 H14 2 0.872807 0.803044 0.569611 11.00000 -1.20000 AFIX 0 C15 1 0.768131 0.811806 0.466228 11.00000 0.06279 0.05294 = 0.08526 0.01046 0.01378 -0.00418 AFIX 43 H15 2 0.767264 0.915773 0.461713 11.00000 -1.20000 AFIX 0 C16 1 0.706845 0.724395 0.408612 11.00000 0.06911 0.06868 = 0.06206 0.01836 0.00561 0.00994 AFIX 43 H16 2 0.665380 0.769626 0.364574 11.00000 -1.20000 AFIX 0 C17 1 0.706027 0.569423 0.415295 11.00000 0.05377 0.06480 = 0.04590 0.00214 0.00201 0.00357 AFIX 43 H17 2 0.663794 0.511749 0.375817 11.00000 -1.20000 AFIX 0 B1 3 0.854179 0.171459 0.333291 11.00000 0.05078 0.07376 = 0.05210 -0.00719 0.01241 0.00564 AFIX 138 H1X 2 0.912784 0.092728 0.372379 11.00000 -1.50000 H1Y 2 0.905991 0.281759 0.332753 11.00000 -1.50000 H1Z 2 0.845219 0.124932 0.272895 11.00000 -1.50000 AFIX 0 C2 1 0.488097 0.179662 0.377011 11.00000 0.04268 0.09893 = 0.06377 -0.02127 0.00490 -0.00956 AFIX 43 H2 2 0.398025 0.158344 0.366058 11.00000 -1.20000 AFIX 0 C3 1 0.541543 0.247929 0.440854 11.00000 0.04096 0.09873 = 0.05863 -0.02220 0.01064 -0.00493 AFIX 43 H3 2 0.495704 0.283846 0.482650 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM cu_nt1362_KB249 in P2(1)/n REM wR2 = 0.1261, GooF = S = 1.052, Restrained GooF = 1.052 for all data REM R1 = 0.0450 for 2647 Fo > 4sig(Fo) and 0.0465 for all 2790 data REM 186 parameters refined using 0 restraints END WGHT 0.0613 0.2908 REM Highest difference peak 0.174, deepest hole -0.150, 1-sigma level 0.034 Q1 1 0.7434 0.3317 0.6023 11.00000 0.05 0.17 Q2 1 0.9319 0.2682 0.3615 11.00000 0.05 0.17 Q3 1 0.7830 0.4214 0.4837 11.00000 0.05 0.17 Q4 1 0.8407 0.2641 0.5985 11.00000 0.05 0.15 Q5 1 0.7784 0.3193 0.5369 11.00000 0.05 0.14 Q6 1 0.7039 0.2726 0.5857 11.00000 0.05 0.14 Q7 1 0.8352 0.5477 0.4939 11.00000 0.05 0.14 Q8 1 0.7826 0.1930 0.5811 11.00000 0.05 0.14 Q9 1 0.7780 0.1787 0.3452 11.00000 0.05 0.13 Q10 1 0.8448 0.0444 0.3092 11.00000 0.05 0.13 Q11 1 0.6026 0.1855 0.4640 11.00000 0.05 0.12 Q12 1 0.5214 0.1240 0.4190 11.00000 0.05 0.12 Q13 1 0.8540 0.2262 0.2698 11.00000 0.05 0.12 Q14 1 0.4609 0.1171 0.2328 11.00000 0.05 0.11 Q15 1 0.8667 0.6676 0.5231 11.00000 0.05 0.11 Q16 1 0.7539 0.5467 0.5219 11.00000 0.05 0.11 Q17 1 0.8300 0.7476 0.4799 11.00000 0.05 0.11 Q18 1 0.7788 0.5196 0.4397 11.00000 0.05 0.10 Q19 1 0.8152 0.1842 0.7039 11.00000 0.05 0.10 Q20 1 0.7337 0.2587 0.7179 11.00000 0.05 0.10 ; _shelx_res_checksum 70386 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.67762(10) 0.25518(12) 0.43316(6) 0.0459(3) Uani 1 1 d . . . . . N2 N 0.59105(11) 0.14686(13) 0.33059(6) 0.0522(3) Uani 1 1 d . . . . . C1 C 0.57329(17) 0.0742(2) 0.25409(9) 0.0731(5) Uani 1 1 d . . . . . H1A H 0.509925 0.130026 0.221331 0.110 Uiso 0.34(2) 1 calc R U P . . H1B H 0.540828 -0.026095 0.260541 0.110 Uiso 0.34(2) 1 calc R U P . . H1C H 0.657457 0.070932 0.230152 0.110 Uiso 0.34(2) 1 calc R U P . . H1D H 0.628882 -0.013451 0.253352 0.110 Uiso 0.66(2) 1 calc R U P . . H1E H 0.597979 0.142670 0.214142 0.110 Uiso 0.66(2) 1 calc R U P . . H1F H 0.481350 0.045643 0.244530 0.110 Uiso 0.66(2) 1 calc R U P . . C4 C 0.70869(12) 0.19291(13) 0.36462(7) 0.0431(3) Uani 1 1 d . . . . . C5 C 0.85365(14) 0.16369(15) 0.59987(8) 0.0542(4) Uani 1 1 d . . . . . H5 H 0.919948 0.128804 0.568722 0.065 Uiso 1 1 calc R U . . . C6 C 0.84528(17) 0.10699(18) 0.67444(9) 0.0683(4) Uani 1 1 d . . . . . H6 H 0.906243 0.034995 0.693296 0.082 Uiso 1 1 calc R U . . . C7 C 0.74762(17) 0.15627(18) 0.72079(9) 0.0656(4) Uani 1 1 d . . . . . H7 H 0.741690 0.117019 0.770813 0.079 Uiso 1 1 calc R U . . . C8 C 0.65795(15) 0.26429(17) 0.69321(8) 0.0598(4) Uani 1 1 d . . . . . H8 H 0.591401 0.297674 0.724585 0.072 Uiso 1 1 calc R U . . . C9 C 0.66717(13) 0.32297(15) 0.61869(7) 0.0516(3) Uani 1 1 d . . . . . H9 H 0.607668 0.397091 0.600636 0.062 Uiso 1 1 calc R U . . . C10 C 0.76468(12) 0.27185(13) 0.57077(7) 0.0431(3) Uani 1 1 d . . . . . C11 C 0.77550(11) 0.32981(14) 0.48808(7) 0.0438(3) Uani 1 1 d . . . . . H11 H 0.864253 0.300582 0.472311 0.053 Uiso 1 1 calc R U . . . C12 C 0.76754(11) 0.49978(15) 0.48023(7) 0.0442(3) Uani 1 1 d . . . . . C13 C 0.83140(13) 0.58987(16) 0.53754(8) 0.0555(4) Uani 1 1 d . . . . . H13 H 0.875129 0.545505 0.581129 0.067 Uiso 1 1 calc R U . . . C14 C 0.83064(15) 0.74445(17) 0.53049(10) 0.0647(4) Uani 1 1 d . . . . . H14 H 0.872807 0.803044 0.569611 0.078 Uiso 1 1 calc R U . . . C15 C 0.76813(15) 0.81181(18) 0.46623(10) 0.0666(4) Uani 1 1 d . . . . . H15 H 0.767264 0.915773 0.461713 0.080 Uiso 1 1 calc R U . . . C16 C 0.70685(16) 0.72439(19) 0.40861(9) 0.0666(4) Uani 1 1 d . . . . . H16 H 0.665380 0.769626 0.364574 0.080 Uiso 1 1 calc R U . . . C17 C 0.70603(14) 0.56942(17) 0.41529(8) 0.0549(4) Uani 1 1 d . . . . . H17 H 0.663794 0.511749 0.375817 0.066 Uiso 1 1 calc R U . . . B1 B 0.85418(16) 0.1715(2) 0.33329(10) 0.0585(4) Uani 1 1 d . . . . . H1X H 0.9128(7) 0.0927(12) 0.3724(5) 0.088 Uiso 1 1 calc R U . . . H1Y H 0.9060(6) 0.2818(11) 0.3328(6) 0.088 Uiso 1 1 calc R U . . . H1Z H 0.84522(17) 0.1249(13) 0.2729(6) 0.088 Uiso 1 1 calc R U . . . C2 C 0.48810(14) 0.1797(2) 0.37701(9) 0.0684(4) Uani 1 1 d . . . . . H2 H 0.398025 0.158344 0.366058 0.082 Uiso 1 1 calc R U . . . C3 C 0.54154(14) 0.2479(2) 0.44085(9) 0.0658(4) Uani 1 1 d . . . . . H3 H 0.495704 0.283846 0.482650 0.079 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0394(5) 0.0564(6) 0.0424(5) -0.0071(4) 0.0055(4) -0.0008(4) N2 0.0489(6) 0.0606(7) 0.0470(6) -0.0097(5) 0.0028(4) -0.0045(5) C1 0.0706(10) 0.0895(12) 0.0586(9) -0.0264(8) -0.0008(7) -0.0105(8) C4 0.0468(7) 0.0428(6) 0.0397(6) 0.0009(5) 0.0034(5) 0.0021(5) C5 0.0526(7) 0.0524(7) 0.0578(8) 0.0001(6) 0.0035(6) 0.0078(6) C6 0.0740(10) 0.0635(9) 0.0670(9) 0.0161(7) -0.0001(7) 0.0095(7) C7 0.0798(10) 0.0668(9) 0.0499(7) 0.0115(6) 0.0011(7) -0.0110(8) C8 0.0657(9) 0.0663(9) 0.0488(7) -0.0088(6) 0.0151(6) -0.0085(7) C9 0.0516(7) 0.0549(7) 0.0487(7) -0.0039(5) 0.0072(5) 0.0056(6) C10 0.0423(6) 0.0445(6) 0.0423(6) -0.0042(5) 0.0015(5) -0.0005(5) C11 0.0364(6) 0.0536(7) 0.0416(6) -0.0051(5) 0.0026(5) 0.0024(5) C12 0.0364(6) 0.0537(7) 0.0431(6) 0.0012(5) 0.0060(5) 0.0003(5) C13 0.0503(7) 0.0587(8) 0.0564(8) 0.0016(6) -0.0053(6) -0.0056(6) C14 0.0578(8) 0.0577(8) 0.0781(10) -0.0038(7) -0.0002(7) -0.0130(6) C15 0.0628(9) 0.0529(8) 0.0853(11) 0.0105(7) 0.0138(8) -0.0042(7) C16 0.0691(9) 0.0687(9) 0.0621(9) 0.0184(7) 0.0056(7) 0.0099(7) C17 0.0538(7) 0.0648(8) 0.0459(7) 0.0021(6) 0.0020(5) 0.0036(6) B1 0.0508(9) 0.0738(11) 0.0521(8) -0.0072(7) 0.0124(7) 0.0056(7) C2 0.0427(7) 0.0989(12) 0.0638(9) -0.0213(8) 0.0049(6) -0.0096(7) C3 0.0410(7) 0.0987(12) 0.0586(8) -0.0222(8) 0.0106(6) -0.0049(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C3 110.18(11) . . ? C4 N1 C11 124.00(10) . . ? C3 N1 C11 125.67(10) . . ? C4 N2 C2 110.72(11) . . ? C4 N2 C1 125.31(12) . . ? C2 N2 C1 123.95(12) . . ? N2 C1 H1A 109.5 . . ? N2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C1 H1D 109.5 . . ? H1A C1 H1D 141.1 . . ? H1B C1 H1D 56.3 . . ? H1C C1 H1D 56.3 . . ? N2 C1 H1E 109.5 . . ? H1A C1 H1E 56.3 . . ? H1B C1 H1E 141.1 . . ? H1C C1 H1E 56.3 . . ? H1D C1 H1E 109.5 . . ? N2 C1 H1F 109.5 . . ? H1A C1 H1F 56.3 . . ? H1B C1 H1F 56.3 . . ? H1C C1 H1F 141.1 . . ? H1D C1 H1F 109.5 . . ? H1E C1 H1F 109.5 . . ? N2 C4 N1 105.00(10) . . ? N2 C4 B1 127.72(11) . . ? N1 C4 B1 127.20(11) . . ? C6 C5 C10 120.90(13) . . ? C6 C5 H5 119.6 . . ? C10 C5 H5 119.6 . . ? C7 C6 C5 120.27(14) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 119.94(14) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 119.95(13) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 120.49(13) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C5 C10 C9 118.44(12) . . ? C5 C10 C11 119.45(11) . . ? C9 C10 C11 122.11(11) . . ? N1 C11 C10 110.99(10) . . ? N1 C11 C12 111.31(9) . . ? C10 C11 C12 114.52(10) . . ? N1 C11 H11 106.5 . . ? C10 C11 H11 106.5 . . ? C12 C11 H11 106.5 . . ? C17 C12 C13 118.01(13) . . ? C17 C12 C11 122.37(11) . . ? C13 C12 C11 119.49(11) . . ? C14 C13 C12 120.88(13) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 120.41(14) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.37(14) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C17 120.75(14) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 120.57(13) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C4 B1 H1X 109.5 . . ? C4 B1 H1Y 109.5 . . ? H1X B1 H1Y 109.5 . . ? C4 B1 H1Z 109.5 . . ? H1X B1 H1Z 109.5 . . ? H1Y B1 H1Z 109.5 . . ? C3 C2 N2 107.05(12) . . ? C3 C2 H2 126.5 . . ? N2 C2 H2 126.5 . . ? C2 C3 N1 107.04(12) . . ? C2 C3 H3 126.5 . . ? N1 C3 H3 126.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.3510(15) . ? N1 C3 1.3790(17) . ? N1 C11 1.4748(15) . ? N2 C4 1.3465(16) . ? N2 C2 1.3712(18) . ? N2 C1 1.4616(17) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 H1D 0.9600 . ? C1 H1E 0.9600 . ? C1 H1F 0.9600 . ? C4 B1 1.5948(19) . ? C5 C6 1.380(2) . ? C5 C10 1.3850(18) . ? C5 H5 0.9300 . ? C6 C7 1.369(2) . ? C6 H6 0.9300 . ? C7 C8 1.380(2) . ? C7 H7 0.9300 . ? C8 C9 1.3866(19) . ? C8 H8 0.9300 . ? C9 C10 1.3899(17) . ? C9 H9 0.9300 . ? C10 C11 1.5165(16) . ? C11 C12 1.5228(18) . ? C11 H11 0.9800 . ? C12 C17 1.3843(17) . ? C12 C13 1.3927(18) . ? C13 C14 1.383(2) . ? C13 H13 0.9300 . ? C14 C15 1.370(2) . ? C14 H14 0.9300 . ? C15 C16 1.372(2) . ? C15 H15 0.9300 . ? C16 C17 1.386(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? B1 H1X 1.112(11) . ? B1 H1Y 1.112(11) . ? B1 H1Z 1.112(11) . ? C2 C3 1.334(2) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N2 C4 N1 -0.02(15) . . . . ? C1 N2 C4 N1 178.94(13) . . . . ? C2 N2 C4 B1 177.13(15) . . . . ? C1 N2 C4 B1 -3.9(2) . . . . ? C3 N1 C4 N2 -0.30(15) . . . . ? C11 N1 C4 N2 -176.00(11) . . . . ? C3 N1 C4 B1 -177.46(14) . . . . ? C11 N1 C4 B1 6.8(2) . . . . ? C10 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -0.7(2) . . . . ? C6 C7 C8 C9 -0.2(2) . . . . ? C7 C8 C9 C10 1.2(2) . . . . ? C6 C5 C10 C9 0.5(2) . . . . ? C6 C5 C10 C11 -179.04(13) . . . . ? C8 C9 C10 C5 -1.4(2) . . . . ? C8 C9 C10 C11 178.16(12) . . . . ? C4 N1 C11 C10 -130.54(12) . . . . ? C3 N1 C11 C10 54.43(17) . . . . ? C4 N1 C11 C12 100.64(13) . . . . ? C3 N1 C11 C12 -74.39(16) . . . . ? C5 C10 C11 N1 99.01(13) . . . . ? C9 C10 C11 N1 -80.50(14) . . . . ? C5 C10 C11 C12 -133.91(12) . . . . ? C9 C10 C11 C12 46.58(16) . . . . ? N1 C11 C12 C17 -17.63(15) . . . . ? C10 C11 C12 C17 -144.54(11) . . . . ? N1 C11 C12 C13 166.65(10) . . . . ? C10 C11 C12 C13 39.74(15) . . . . ? C17 C12 C13 C14 1.43(19) . . . . ? C11 C12 C13 C14 177.34(13) . . . . ? C12 C13 C14 C15 -0.8(2) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C14 C15 C16 C17 0.9(2) . . . . ? C13 C12 C17 C16 -0.92(19) . . . . ? C11 C12 C17 C16 -176.71(12) . . . . ? C15 C16 C17 C12 -0.2(2) . . . . ? C4 N2 C2 C3 0.33(19) . . . . ? C1 N2 C2 C3 -178.64(16) . . . . ? N2 C2 C3 N1 -0.5(2) . . . . ? C4 N1 C3 C2 0.51(19) . . . . ? C11 N1 C3 C2 176.12(13) . . . . ?